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Record Information
Version1.0
Creation Date2016-09-30 22:31:20 UTC
Update Date2020-06-04 20:20:16 UTC
BMDB IDBMDB0000479
Secondary Accession Numbers
  • BMDB00479
Metabolite Identification
Common Name3-Methylhistidine
DescriptionN(pros)-Methyl-L-histidine, also known as 3-methylhistidine, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N(pros)-Methyl-L-histidine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N(pros)-Methyl-L-histidine exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acidChEBI
3-Methyl-L-histidineChEBI
N(Pai)-methyl-L-histidineChEBI
N-pros-Methyl-L-histidineChEBI
Tau-methylhistidineChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoateGenerator
3-N-Methyl-L-histidineHMDB
L-3-MethylhistidineHMDB
N(Pi)-methyl-L-histidineHMDB
N(pros)-Methyl-L-histidineHMDB
N3-Methyl-L-histidineHMDB
Pi-methyl-L-histidineHMDB
Tau-methyl-L-histidineHMDB
3-Methylhistidine hydrideHMDB
N(Tau)-methylhistidineHMDB
3-Methylhistidine dihydrochlorideHMDB
N Tau-methylhistidineHMDB
3-MethylhistidineChEBI
Chemical FormulaC7H11N3O2
Average Molecular Weight169.1811
Monoisotopic Molecular Weight169.085126611
IUPAC Name(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional Name3,methylhistidine
CAS Registry Number368-16-1
SMILES
[H][C@](N)(CC1=CN=CN1C)C(O)=O
InChI Identifier
InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
InChI KeyJDHILDINMRGULE-LURJTMIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility200 mg/mL at 25 °CBEILSTEIN
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.9ALOGPS
logP-3.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.96 m³·mol⁻¹ChemAxon
Polarizability16.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-9500000000-ab7d6324146b8775fe50View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9400000000-42443c78fdfca9db1926View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-2900000000-15f0e43eb0d06e7f3ef3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9200000000-5a1ab4d052e6ba4a76e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0002-9000000000-c1951c88c84885804fb6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-4e0fea0fe9b1142db07bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0592-4900000000-ee1bce969d650e9fcfbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-9200000000-1ad733cdcfa4db4fe3b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0002-9000000000-a87ff5cc0642ea3af69cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0002-9000000000-28a73708493f968c2ac6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9800000000-6565ccf96757ef3bc08fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3cbd02f5b6c4e6e64eb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0900000000-e6ce7548fd6f09e2098fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3cbd02f5b6c4e6e64eb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-2d351351f285b2188710View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0592-4900000000-ee1bce969d650e9fcfbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9200000000-1ad733cdcfa4db4fe3b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-2ed34e7b458d9f8c092fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-c1b8a62adc15b80955c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9800000000-6565ccf96757ef3bc08fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-1ca24429b22e547d10d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-4cafc4698b6e3649ce7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-ef0c8b716935df30c508View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-8a91a6a64bb07285c36dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-4900000000-4ad91c6f55caf69120e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05di-9300000000-ea67f38340a4b7ef8e11View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14 +/- 2 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified25 +/- 5 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Longissimus Thoracis MuscleDetected and Quantified35 +/- 8 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
MilkDetected and Quantified103 - 151 uMNot SpecifiedNot SpecifiedNormal details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified2 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Semimembranosus MuscleDetected and Quantified35 +/- 9 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified19 +/- 4 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000479
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB093613
KNApSAcK IDNot Available
Chemspider ID58494
KEGG Compound IDC01152
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylhistidine
METLIN ID5466
PubChem Compound64969
PDB IDNot Available
ChEBI ID27596
References
Synthesis ReferenceOhba, Masashi; Mukaihira, Takafumi; Fujii, Tozo. Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines. Chemical & Pharmaceutical Bulletin (1994), 42(9), 1784-90.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

General function:
Involved in histone binding
Specific function:
Arginine methyltransferase that can catalyze the formation of both omega-N monomethylarginine (MMA) and asymmetrical dimethylarginine (aDMA), with a strong preference for the formation of aDMA. Preferentially methylates arginyl residues present in a glycine and arginine-rich domain and displays preference for monomethylated substrates. Specifically mediates the asymmetric dimethylation of histone H3 'Arg-2' to form H3R2me2a. H3R2me2a represents a specific tag for epigenetic transcriptional repression and is mutually exclusive with methylation on histone H3 'Lys-4' (H3K4me2 and H3K4me3). Acts as a transcriptional repressor of various genes such as HOXA2, THBS1 and TP53 (By similarity). Repression of TP53 blocks cellular senescence (By similarity). Also methylates histone H2A and H4 'Arg-3' (H2AR3me and H4R3me, respectively). Acts as a regulator of DNA base excision during DNA repair by mediating the methylation of DNA polymerase beta (POLB), leading to the stimulation of its polymerase activity by enhancing DNA binding and processivity. Methylates HMGA1. Regulates alternative splicing events. Acts as a transcriptional coactivator of a number of steroid hormone receptors including ESR1, ESR2, PGR and NR3C1. Promotes fasting-induced transcriptional activation of the gluconeogenic program through methylation of the CRTC2 transcription coactivator. Methylates GPS2, protecting GPS2 from ubiquitination and degradation. Methylates SIRT7, inhibiting SIRT7 histone deacetylase activity and promoting mitochondria biogenesis (By similarity).
Gene Name:
PRMT6
Uniprot ID:
Q5E9L5
Molecular weight:
41868.0
Reactions
L-Histidine + S-Adenosylmethionine → 3-Methylhistidine + S-Adenosylhomocysteinedetails
General function:
Amino acid transport and metabolism
Specific function:
Hydrolyzes a variety of dipeptides including L-carnosine but has a strong preference for Cys-Gly. Catalyzes the production of N-lactoyl-amino acids from lactate and amino acids by reverse proteolysis.
Gene Name:
CNDP2
Uniprot ID:
Q3ZC84
Molecular weight:
52655.0
Reactions
Anserine + Water → Beta-Alanine + 3-Methylhistidinedetails